The reaction of chlorohosphates with strong bases: Synthesis and characterization of the phosphonate salts

Tetrahedron Letters

Volumn 39, Issue 13, 1998, Pages 1819-1822

  Vijjulatha, M ^a   Praveen Kumar, K ^a   Kumara Swamy, K C ^a   Vittal, J J ^b  

^a UNIVERSITY OF HYDERABAD   (India)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; ISOLATION PROCEDURE; PHOSPHATE METABOLISM; PROTEIN STABILITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0032568227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00096-3     Document Type: Article

References (17)

1. 1. Corriu, R. J. P.; Lanneau, G. F.; Leclercq, D. F., Tetrahedron 1989, 45, 1959.
2. 2. Lanneau, G. F. Phosphorus and Sulfur 1986, 27, 51.
3. 3. Y. Hayakawa in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds; Volume 6 ; Winterfeldt, E.(Volume Ed.), Pergamon: Oxford, 1991, p. 602.
4. 4. a) Meisel, M.; Donath, C. Phosphorus Sulfur, Silicon 1992, 64, 63;
5. b) Meisel, M Phosphorus, Sulfur, Silicon 1993, 76, 99.
6. 5. a) Teichmann, H.; Wilbrandt, D.; Schulz, J. Phosphorus, Sulfur, Silicon 1990, 49/50, 251.
7. b) Teichmann, H.; Schulz, J.; Costisella, B.; Habisch, D. Z. Anorg. Allgem. Chem. 1991, 606, 233.
8. 6. Quast, H.; Heuschmann, M. J. Chem. Soc., Chem. Commun. 1979, 390.
9. 7. Quin, L. D. Coord. Chem. Rev. 1994, 137, 525.
10. 1(I > 2σ (1)) 0.0483, wR2 = 0.1173 (SHELXTL, Version 5.03). Two orientations were found for C(7); only one of these is shown in the Fig. 1
11. 9. Reed, R.; Reau, R.; Dahan, F.; Bertrand, G. Angew. Chem. Int Edn. Engl. 1993, 32, 399.
12. 10. Hermecz, I. Adv. Heterocycl. Chem. 1987, 42, 83.
13. 11. See, for example, Merckling, F. A.; Rüedi, P. Tetrahedron Lett. 1996, 37, 2217.
14. 1 (I > 2 σ (I)] = 0.0698; wR2 = 0.1811 (SHELXL-97). More details including the ORTEPs are available from the authors.
15. 13 Edmundson, R. S.; Bartle, K. D. Tetrahedron 1965, 21, 1701.
16. 2: C, 72.95, H, 8.86. Found: C, 72.77, H, 9.36.
17. 31P NMR peak for the mixture [-4.2 ppm in the reaction with DBN] was different from any of the two peaks [-6.8, -12.0] observed in the reaction of 1 with DBN. This, in conjunction with the fact that the concentration of the pyrophosphate increases over a period of time in the reaction of 1 with N-methylimidazole or imidazole or 4-dimethylaminopyridine, suggests the involvement of the betaines of type III. This aspect is currently under investigation.